3-[[(1R,3R,4R,7S)-1-[[Bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile

Base Information

• Chemical Name: 3-[[(1R,3R,4R,7S)-1-[[Bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile
• CAS No.: 206055-75-6
• Molecular Formula: C₄₁H₄₉N₄O₉P
• Molecular Weight: 772.835
• European Community (EC) Number: 686-262-2
• Nikkaji Number: J1.747.417K
• Mol file: 206055-75-6.mol

Synonyms:206055-75-6;3-[[(1R,3R,4R,7S)-1-[[Bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile;DMTr-LNA-5MeU-3-CED-phosphoramidite;(1R,3R,4R,7S)-1-((Bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl (2-cyanoethyl) diisopropylphosphoramidite;SCHEMBL1099028;EX-A7174B;MFCD22373376;AKOS040740771;BP-40025;A897818;5'-O-(4,4'-Dimethoxytrityl)-LNA-thymidine-3'-cyanoethyl phosphoramidite;5'-O-(4, 4'-dimethoxytrityl)-2'-O-4'-C-Locked-thymidine-3'-cyanoethyl Phosphoramidite

Chemical Property of 3-[[(1R,3R,4R,7S)-1-[[Bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile

Chemical Property:

• PKA: 9.46±0.10(Predicted)
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 17
• Exact Mass: 772.32371615
• Heavy Atom Count: 55
• Complexity: 1350

Purity/Quality:

98%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2C3C(C(O2)(CO3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)OP(N(C(C)C)C(C)C)OCCC#N
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2[C@H]3[C@@H]([C@@](O2)(CO3)COC(C4=CC=CC=C4)(C5=CC=C(C=C5)OC)C6=CC=C(C=C6)OC)OP(N(C(C)C)C(C)C)OCCC#N
• Uses: DMT-?locT Phosphoramidite is a locked-nucleic Acid (LNA) oligonucleotide which is used in oligonucleotide synthesis via protected groups.

Technology Process of 3-[[(1R,3R,4R,7S)-1-[[Bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile

There total 31 articles about 3-[[(1R,3R,4R,7S)-1-[[Bis(4-methoxyphenyl)-phenylmethoxy]methyl]-3-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dioxabicyclo[2.2.1]heptan-7-yl]oxy-[di(propan-2-yl)amino]phosphanyl]oxypropanenitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + 1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methylpyrimidine-2,4-dione (206055-71-2) → (1R,3R,4R,7S)-3-(thymine-1-yl)-1-(4,4′-dimethoxytrityloxy)-7-(2-cyanoethoxy(diisopropylamino)phosphinoxymethyl)-2,5-dioxabicyclo[2.2.1]heptane (206055-75-6)

Guidance literature:

With 4,5-dicyano-1H-imidazole; In dichloromethane; acetonitrile; at 20 ℃; for 2h;

DOI:10.1055/s-2002-25756

Reference yield: 70.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methylpyrimidine-2,4-dione (206055-71-2) → (1R,3R,4R,7S)-3-(thymine-1-yl)-1-(4,4′-dimethoxytrityloxy)-7-(2-cyanoethoxy(diisopropylamino)phosphinoxymethyl)-2,5-dioxabicyclo[2.2.1]heptane (206055-75-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1039/a708608c

Reference yield:

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose (63593-03-3) → (1R,3R,4R,7S)-3-(thymine-1-yl)-1-(4,4′-dimethoxytrityloxy)-7-(2-cyanoethoxy(diisopropylamino)phosphinoxymethyl)-2,5-dioxabicyclo[2.2.1]heptane (206055-75-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) NaH / 1.) DMF, -5 deg C, 1.5 h, 2.) room temperature, 3 h

2: 90 percent / pyridine / 3 h / Ambient temperature

3: 80percent AcOH / 4 h / 90 °C

4: pyridine / 72 h / Ambient temperature

5: 1.) N,O-bis(trimethylsilyl)acetamide, 2.) TMS-triflate / 1.) CH₃CN, reflux, 1 h, 2.) 65 deg C, 2 h

6: 97 percent / NaOMe / methanol / 0.17 h / Ambient temperature

7: 1.) pTsCl, 2.) NaH / 1.) Py, room temperature, 20 h, 2.) DMF, 0 deg C, 72 h

8: 98 percent / H₂ / Pd(OH)2/C / ethanol / 4 h / Ambient temperature

9: 93 percent / pyridine / 2 h / Ambient temperature

10: 70 percent / iPr₂EtN / CH₂Cl₂ / 1 h

With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate; hydrogen; sodium methylate; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; p-toluenesulfonyl chloride; palladium dihydroxide; In pyridine; methanol; ethanol; dichloromethane;

DOI:10.1016/S0040-4020(98)00094-5

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methylpyrimidine-2,4-dione

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

2',3'-O-benzylidene-4'-(p-toluenesulfonyloxymethyl)uridine

Downstream raw materials:

C₅₂H₆₂N₅O₁₆PSi